Phenyl isocyanate → HCID 58869069, compound

HRID 1623140Notes

Reaction equation

HRID 1623140 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:22][CH2:23][CH3:24])[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][O:20][CH3:21])[C:10]=2[C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.C(N(CC)CC)C.[C:32]1([N:38]=[C:39]=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>ClCCl.C(=O)(O)[O-].[Na+]>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:22][CH2:23][CH3:24])[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]([O:20][CH3:21])[C:39]([NH:38][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:40])[C:10]=2[C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 86612245HCID 86612245, compound2×

Product 1

HCID 58869069HCID 58869069, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-10 °C

Procedure

The preparation of 4-(4-amino-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl O-methylhydroxylamine is described in Parts A-H of Example 1. Triethylamine (0.23 mL, 1.64 mmol) was added to a solution of 4-(4-amino-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl O-methylhydroxylamine (0.45 g, 1.37 mmol) in dichloromethane (10 mL) cooled to −10° C. Phenyl isocyanate (0.15 mL, 1.37 mmol) was added to the reaction mixture and it was allowed to warm to 0° C. over 1 hour. The reaction mixture was diluted with dichloromethane (50 mL) and saturated sodium bicarbonate (40 mL) and the phases were separated. The aqueous layer was extracted with dichloromethane (30 mL) and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford a yellow material. The material was purified by HPFC (0-25% CMA in chloroform) and recrystallized from acetonitrile to afford an off-white solid. The solid was dried at 100° C. under high vacuum to afford 0.388 g of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-N-methoxy-N′-phenylurea as an off-white powder, mp 155-156° C. Anal. calcd for C24H29N7O2: C, 64.41; H, 6.53; N, 21.91. Found: C, 64.20; H, 6.64; N, 21.93.

Workup

  1. temperatureto warm to 0° C. over 1 hour
  2. customthe phases were separated
  3. extractionThe aqueous layer was extracted with dichloromethane (30 mL)
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford a yellow material
  8. customThe material was purified by HPFC (0-25% CMA in chloroform)
  9. customrecrystallized from acetonitrile
  10. customto afford an off-white solid
  11. customThe solid was dried at 100° C. under high vacuum

Sources & evidence

ORD record
ord-89ce517c4a9d4447b009ea8e29a3b13c
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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